I rolled down my car window to see the Starbucks menu better in the foggy morning air. I never remember the name they use for the extra-large drink. Venti. With a free drink on my card, I could splurge and go big. Then I glanced in my rearview mirror. An older model Buick had pulled up behind me with two women in it wearing head coverings. Would they go big and get Ventis too? My hand shook with giddiness as I put the car in drive to pull up to the window. I was more excited about what I was about to do for those women behind me than I was about the Venti Salted Caramel Mocha the barista handed me through the window.

My completion of the October Bucket List Life Dare to commit a random act of kindness might sound cliché. But I have always wanted to surprise someone by paying for their order somewhere. So that’s what I did.

The funny thing about it was how much the barista at the drive-thru window thanked me. It was a dreary morning, so I had hoped to make someone’s day a bit brighter with this treat. What I hadn’t expected was that it would start with the barista. It was also serendipitous that I had the free drink on my card for myself. And that I’d made a bit of extra cash that week selling an old Halloween costume. A confluence of events that set the stage for my paying-it-forward adventure.

Here is what impacted me most about taking the step to actually pay for a stranger’s order: I was living out the story I have been wanting to tell. You see, what has kept me from doing it before was the story I have always told myself about myself – the story that said I’m not one of those people who does that sort of thing. Even though I have always wanted to do it. And so paying for the order of the person in line behind me at the Starbucks drive-thru was more than just a feel-good gesture to complete the month’s dare goal. It served as a means of being myself more fully. Living out who I want to be.

Maybe that part shouldn’t have surprised me. After all, I believe very strongly in the concept of making bucket lists because of how they help us ground ourselves in our identities and let us live out who we were created to be. But I hadn’t seen how sometimes we can hamper our own progress by simply buying into the notion that we aren’t, or can’t be, the people we most want to be.

For some more inspiration on paying it forward (and living the story you want to tell), check out what one man has done at his pizza shop in Philadelphia.

Did you complete the October Bucket List Life Dare? If so, how did it go? If not, why not jump in now – just because it’s not October, doesn’t mean it’s too late. Chime in on the comments below to share your story (or the one you want to live into).

In July I dared readers to step out and conquer a bucket list goal that required them to let go. To be wildly free. Something like dancing in the rain.

For me that expression of whimsical freedom came in the form of sitting out on my roof eating ice cream sandwiches with my kids – a daring bit of fun that always appealed to me, while at the same time sort of freaking me out. I put it on my bucket list long ago in hopes that one day I would get the courage to do it.

In response to the dare, I pledged to take my kids out on our roof for an ice cream treat by the end of July… And I did it (just barely before the end of the month)!

It was a sultry evening, thick with late July heat and humidity, but overcast enough that the roof wasn’t too hot to sit on, with a gentle breeze that stirred the warm air around.

I opened the window screen in my office, placed a stepstool under the window, and hoisted myself into the opening, one leg outside, straddling the ledge. Somehow climbing the rest of the way out became a sort of human origami act, me folding myself in half to duck out the window, while testing different bent configurations of my limbs in an effort to fit through without falling. I tried and got stuck. Tried again. And finally managed to squeeze through and pull my other leg over the ledge.

It seemed like it should have been easier, especially when each of my three girls popped out the window behind me with brisk efficiency. In my defense, having an ice cream sandwich in one hand did add a challenge to the process. That and a fear of heights.

Once outside all four of us lined up along the low roof above our garage, eating, chatting and people watching. I kept waiting for passers-by to spot us, but no one looked up in our direction. Perhaps it didn’t occur to them to expect anyone to be up where we were. But it seemed strange to me to see our neighbors pass by close enough to hear their conversation and yet not have them notice us. I’m used to the vantage from our driveway where we sometimes sit. There we share greetings with most who walk by.

As it was, it was a relatively quiet night. Very few cars, a handful of bikers, and a small number of walkers. The emptiness along our street wasn’t surprising though, since our little city tends to empty out in late July as swim, baseball and softball seasons end, and families finally take their vacations.

After devouring our ice creams we sat there for a bit longer, enjoying the night and the view. One of my girls suggested bringing a game out to play. But that went beyond my comfort zone. I guess I hid my anxiety at being up high a little too well.

I’m glad we did it, though. That simple act – eating ice cream sandwiches on the roof – whimsical as it was, made for a memorable evening. I can see us doing that again next summer and the one after.

Just don’t expect to see me walking around out there. I’ll be the one on the end, back pressed firmly against the house.

This month’s bucket list life dare was to be a tourist in your own region. When you live somewhere like Chicagoland, finding new places to explore doesn’t take much. In our case, the destination was Eataly, Mario Batali’s Italian marketplace concept store (locations in Rome, New York & Chicago). It seemed appropriate in light of my big dream bucket list goal to visit Tuscany. And I figured my cheese- and pasta-loving family would be game.

We set off for our mostly-indoor adventure on Saturday morning, since rain was in the forecast… until it wasn’t. No matter, traffic was light and the sidewalks were humming with shoppers when we arrived in the city. We could have parked on the street (plenty of spots were open), but the two-hour limit made us unsure. How big was Eataly? And if we ate lunch there, how long would we be? We opted for the parking garage across the street, not realizing Eataly offers valet parking for around the same cost.

Turns out, we could have parked on the street for how long we spent there. Not that we didn’t enjoy it, but my biggest takeaway from this bucket list outing was that some experiences are destinations unto themselves and others are not. This one was not. Unless you are planning a special Italian dinner and want to get exactly the right ingredients. Because that, my friends, is what Eataly is all about: authentic Italian cooking. Which, of course, you could learn simply by reading their tag line: “We cook what we sell, and we sell what we cook.”

Eataly is a cross between food court and grocery store. Here are some highlights from our experience:

Cooking gadgets: on the first floor they sell cookware and gadgets. We spent some time browsing the displays. They carry fun and innovative products, many (all?) Italian made. The gadgets are stocked in small bins with a labeled display above them telling you what is what. I admired the pasta cutters with Katherine, my fourteen-year-old, whose goal this summer is to make homemade pasta

Chocolates, biscotti, coffees. Eataly carries a terrific variety – this is probably what tempted me most. But, as I came discover with the rest of the store, I was too overwhelmed by the options to decide. I made a note to myself that once I’ve been to Italy to try some of them, I’ll know where to stock up back home. Unfortunately, contrary to what I had heard about Eataly, we only came across one sample in the store (near guest services). Maybe we were there too early.

Big wheels of cheese. Cheese, cheese, and more cheese. Most of them molto caro (very expensive). $55/lb? Not even my cheese aficionado husband could stomach that. It was fun to browse the cheese cases though, and maybe if we had a particular use for a certain cheese we would have gotten some.

Fresh focaccia. We stopped to watch bread dough being kneaded in the on-site bakery. Briefly. The bakers seemed to be self-conscious about being watched, which is a little odd for someone working behind a glass wall that invites shoppers to take a peek. Whatever. They had a variety of sweet and savory fresh focaccias available. This intrigued me because I had only ever tasted focaccia made for dipping in oil. Katherine, Evelyn & I bought a blueberry sweet focaccia and Mike picked up a prosciutto and mozzarella piece. We stood at a bar-height table nearby to munch them. A layer of sugar topped the sweet focaccia and piles of blueberries filled in the dents. The bread itself balanced out the sweetness perfectly. And the mozzarella focaccia had the right blend of flavors too. On another visit I’ll gladly try the other varieties of focaccia. We could have lunched on focaccia, but we all preferred it as a “snack.”

Gelato! Eataly offers an array of dining options: a casual pasta place, a fine Italian restaurant, a sandwich spot, and more. Whether it was from being overwhelmed by all the options or simply turned off by the cost, none of us felt like dining there. I decided it would suit me more to go there with a bunch of girlfriends. But just because we hadn’t eaten lunch yet didn’t mean we had to pass up dessert. My girls turned down buying crepes at the Nutella bar, reasoning that we could make our own at home. True. Instead we split a two-scoop gelato. Wow! If I had known how amazing Eataly’s gelato is, I would have gotten my own. The salted caramel gelato tasted like fresh caramel. And the chocolate – if you closed your eyes you would think you were enjoying a fine piece of European chocolate. No artificial flavors about this gelato.

After about 90 minutes we had our fill of Eataly. Check that one off the bucket list! But we were still hungry for lunch. So at Mike’s suggestion, we trekked a bit farther north in the city to enjoy a barbecue lunch out on the patio of Smoque.

What can I say? We’re suckers for the familiar. And now I know the next time I’m in Chicago’s Gold Coast neighborhood I should bring my grocery list for a side trip to Eataly. I just might get my own scoop of gelato while I’m at it!

Did you take the dare to be a tourist in your own region? If so, what were the results? If not, don’t worry. Another dare is coming in July.

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Families today struggle for quality time together. I help them clarify their priorities into a list that motivates and energizes them to do authentically meaningful things together. Families who have created a family bucket list enjoy better family time, experience stronger relationships and live less stressed lives.

I'm a parenting journalist and mom of three who knows what it's like trying to keep a household running and still find quality time with the husband and kids. Family bucket lists are key. I hope you'll stick around to learn how.